1-Benzyl-2-bromobenzene → HCID 12831588, compound

HRID 1446815Notes

Reaction equation

HRID 1446815 reaction equation
C([Li])CCC.[CH:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[C:18](Br)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[O:20]1[C:24]2([CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]2)[O:23][CH2:22][CH2:21]1>CCCCCC.C1COCC1>[C:9]1([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:27]2([OH:30])[CH2:28][CH2:29][C:24]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:25][CH2:26]2)[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 130611-Benzyl-2-bromobenzeneHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 178418339Butyllithium

Product 1

HCID 12831588HCID 12831588, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

26.25 ml of 2.4 molar solution of n-butyllithium in n-hexane is added dropwise with stirring at -50° to -40° C. under dry nitrogen to a solution of 10.87 g of 2-bromodiphenylmethane in 25 ml of dry THF. The mixture is stirred at -50° to -40° C. for one hour after addition is completed. A solution of 6.30 g of 1,4-dioxaspiro(4.5)decan-8-one in 20 ml of dry THF is added dropwise at -50° to -40° C. This mixture is stirred overnight (16 hours) at -70° C. to +10° C., and quenched with 50 ml of water. The organic phase is diluted with 100 ml of ether and washed three times with 50 ml portions of water. The aqueous phase and the washing water are extracted with 100 ml of CH2Cl2, which is washed twice with 50 ml portions of water. The combined organic phases are dried over Na2SO4 and evaporated to an oil. This oil is treated with ether/hexane (20 ml/50 ml) mixture to give 6.0 g (45.8%) yield of crystalline product which is recrystallized from ether/hexane (10 ml/40 ml) to provide 5.53 g (42.2% yield) of 8-[2-(phenylmethyl)phenyl]-1,4-dioxaspiro(4.5)decan-8-ol, m.p. 97°-98° C.

Workup

  1. additionafter addition
  2. stirringThis mixture is stirred overnight (16 hours) at -70° C. to +10° C.
  3. customquenched with 50 ml of water
  4. additionThe organic phase is diluted with 100 ml of ether
  5. washwashed three times with 50 ml portions of water
  6. extractionThe aqueous phase and the washing water are extracted with 100 ml of CH2Cl2, which
  7. washis washed twice with 50 ml portions of water
  8. dry with materialThe combined organic phases are dried over Na2SO4
  9. customevaporated to an oil
  10. additionThis oil is treated with ether/hexane (20 ml/50 ml) mixture
  11. customto give 6.0 g (45.8%) yield of crystalline product which
  12. customis recrystallized from ether/hexane (10 ml/40 ml)

Sources & evidence

ORD record
ord-d79ce4f1086c4123a371262a76d299e7
Source dataset
uspto-grants-1982_02
Patent number
US04313959

Reaction notes

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