3-(1-Adamantyl)-4-methoxybenzoic acid → HCID 19068253, compound

HRID 1957686Notes

Reaction equation

HRID 1957686 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]12([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=3[O:26][CH3:27])[C:20](O)=[O:21])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[C:7]12([C:17]3[CH:18]=[C:19]([CH2:20][OH:21])[CH:23]=[CH:24][C:25]=3[O:26][CH3:27])[CH2:8][CH:9]3[CH2:15][CH:13]([CH2:12][CH:11]([CH2:10]3)[CH2:16]1)[CH2:14]2

Participants

5

Reactant 3

HCID 52965033-(1-Adamantyl)-4-methoxybenzoic acidHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydride

Product 1

HCID 19068253HCID 19068253, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8 g (0.2 mol) of lithium aluminum hydride and 50 ml of anhydrous THF were introduced into a three-necked flask under a stream of nitrogen. A solution of 28.6 g (0.1 mol) of 3-(1-adamantyl)-4-methoxybenzoic acid in 260 ml of anhydrous THF was added dropwise and the mixture was heated at reflux for 16 hours. The reaction medium was cooled and hydrolyzed with 14.4 ml of sodium potassium tartrate solution. The salt was filtered off. The filtrate was evaporated and the solid obtained was triturated from hexane, filtered off and dried. 26.2 g (96%) of the expected benzyl alcohol, having a melting point of 134°-5° C., were recovered.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe salt was filtered off
  4. customThe filtrate was evaporated
  5. customthe solid obtained
  6. customwas triturated from hexane
  7. filtrationfiltered off
  8. customdried
  9. customwere recovered

Sources & evidence

ORD record
ord-481dbe6dc6ff4e09bc37d4094a44e207
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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