Benzaldehyde → HCID 9838153, compound

HRID 2229866Notes

Reaction equation

HRID 2229866 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:10][CH3:11].CC1(C)CCCC(C)(C)N1.C([Li])CCCCC.[CH:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCCCCC.C1COCC1>[F:8][C:7]1[C:2]([F:1])=[C:3]([O:9][CH2:10][CH3:11])[CH:4]=[CH:5][C:6]=1[CH:29]([OH:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 130352,2,6,6-TetramethylpiperidineHCID 27829281-Ethoxy-2,3-DifluorobenzeneHCID 178506865HCID 178506865, compound

Product 1

HCID 9838153HCID 9838153, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1.1 kg/h of a 1M solution of 2,3-difluorophenetole containing 10 mol % of 2,2,6,6-tetramethylpiperidine were introduced into a continuous-flow reactor and mixed with 0.4 kg/h of a 2.5M solution of hexyllithium in hexane at −35° C. After the mixture had passed through the reaction zone, 0.28 kg/h of a 4.7M solution of benzaldehyde in THF were mixed in. After the reaction had finished, the product was collected and worked up in the customary manner, giving 2,3-difluoro-4-ethoxy-α-phenylbenzyl alcohol. The conversion based on the starting compound was 97%.

Workup

  1. additionwere mixed in
  2. customthe product was collected

Sources & evidence

ORD record
ord-deffde1f536d484fb9d82b96178e0ab7
Source dataset
uspto-grants-2002_07
Patent number
US06420584B1

Reaction notes

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