Water → HCID 53819422, compound

HRID 1651058Notes

Reaction equation

HRID 1651058 reaction equation
[O:1]=[C:2]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH2:3]1.[CH3:18][Li].O>C(OCC)C>[OH:1][C:2]1([CH3:18])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 283964HCID 283964, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 53819422HCID 53819422, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 5-oxo-dibenzo[a,e]cyclooctene (10.0 g) in dry diethyl ether at 0° C. under nitrogen, was added over 5 minutes, through a canula, a solution of methyl lithium (40 ml of a 1.4M solution in diethyl ether). After a further 10 minutes stirring water (40 ml) was added cautiously and the separated aqueous layer discarded. The organic layer was washed with water. then dried and evaporated. Crystallisation from diethyl ether/hexane gave the pure alcohol (6.2 g), mp 108°-109° C.

Workup

  1. additionwas added cautiously
  2. washThe organic layer was washed with water
  3. customthen dried
  4. customevaporated
  5. customCrystallisation from diethyl ether/hexane

Sources & evidence

ORD record
ord-37c4da8d0fa544a0b7dfecf4d9b24fec
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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